Shanpanootols G and H, Diterpenoids from the Rhizomes of Kaempferia pulchra Collected in Myanmar and Their Vpr Inhibitory Activities

Chem Pharm Bull (Tokyo). 2021;69(9):913-917. doi: 10.1248/cpb.c21-00326.

Abstract

Two new trihydroxy derivative of Δ8(14),15-isopimarane diterpenoids, shanpanootols G (1) and H (2), along with three known analogues were isolated from the ethyl acetate-soluble extract of Kaempferia pulchra rhizomes collected in Shan State of Myanmar. The structures of these compounds including their absolute configurations were elucidated by the combination of one dimensional (1D) and 2D-NMR spectroscopic methods, high resolution mass spectrometric technique, and the experimental and the calculated electronic circular dichroism (ECD) data. The isopimarane diterpenoids (1-5) were tested for their Viral protein R (Vpr) inhibitory activities against TREx-HeLa-Vpr cells. Shanpanootol H (2) and (1R,2S,5S,9R,10S,13R)-1,2-dihydroxypimara-8(14),15-dien-7-one (4) exhibited anti-Vpr activities at the 5 µM treated dose.

Keywords: Kaempferia pulchra; TREx-HeLa-Vpr cell; Viral protein R (Vpr) inhibitory activity; shanpanootol G; shanpanootol H; Δ8(14),15-isopimarane diterpenoid.

MeSH terms

  • Diterpenes / chemistry
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology*
  • Molecular Conformation
  • Myanmar
  • Rhizome / chemistry*
  • Zingiberaceae / chemistry*
  • vpr Gene Products, Human Immunodeficiency Virus / antagonists & inhibitors*
  • vpr Gene Products, Human Immunodeficiency Virus / metabolism

Substances

  • Diterpenes
  • vpr Gene Products, Human Immunodeficiency Virus